Methyl vinyl sulfone → HCID 66958902, compound

HRID 2283922Notes

Reaction equation

HRID 2283922 reaction equation
[NH2:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4]1[N:8]([CH2:9][CH3:10])[N:7]=[C:6]([C:11]#[N:12])[C:5]=1[Br:13].[CH:16]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH2:17]>C1(C)C=CC=CC=1>[Br:13][C:5]1[C:6]([C:11]#[N:12])=[N:7][N:8]([CH2:9][CH3:10])[C:4]=1[CH2:3][C:2]([CH3:14])([NH:1][CH2:17][CH2:16][S:18]([CH3:21])(=[O:20])=[O:19])[CH3:15]

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 66959075HCID 66959075, compound

Product 1

HCID 66958902HCID 66958902, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(2-amino-2-methylpropyl)-4-bromo-1-ethyl-1H-pyrazole-3-carbonitrile (4.1 g, 15.1 mmol) and methyl vinyl sulfone (3.2 g, 30.2 mmol) in toluene (30 mL) was heated at reflux for 15 hours, allowed to cool to room temperature, and concentrated under reduced pressure. The crude product was purified twice by column chromatography on silica gel (eluting first with 5% methanol in dichloromethane and secondly with ethyl acetate) to provide 2.75 g of 4-bromo-1-ethyl-5-(2-methyl-2-{[2-(methylsulfonyl)ethyl]amino}propyl)-1H-pyrazole-3-carbonitrile as a colorless oil.

Workup

  1. temperatureat reflux for 15 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified twice by column chromatography on silica gel (
  4. washeluting first with 5% methanol in dichloromethane and secondly with ethyl acetate)

Sources & evidence

ORD record
ord-8142c95a73f949e4aca8877a7d184d9b
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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